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Waylon Arnold Jennings (June 15, 1937 ? February 13, 2002) was a respected and influential American country music singer and guitarist, born in Littlefield, Texas.

He taught himself to play guitar at age eight, and formed his first band two years later. He worked as a DJ throughout his teen years, dropping out of high school to pursue a career in music. During his time working as a DJ, he met and befriended Buddy Holly.

On the night of February 3, 1959 (The Day the Music Died) the airplane carrying Holly, Ritchie Valens and J.P. Richardson (aka The Big Bopper) crashed outside of Mason City, Iowa, killing all passengers. Jennings had given his seat to Richardson, who had the flu and desperately needed rest. In his 1996 autobiography, Jennings admitted for the first time that in the years afterward, he felt severe guilt and responsibility for the crash. After Jennings gave up his seat, Holly had jokingly told him that he hoped the tour bus would stall. Jennings replied, with equal jocularity, that he hoped the plane would crash; these words would haunt him for years.